Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems

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	Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems
	Shang, Jun-Yan 1; Li L(李莉)1; Lu YX(卢一新)2,3; Yang KF(杨科芳)1; Xu LW(徐利文)1,4
刊名	Synthetic Communications
	2014
卷号	44 期号:1 页码:101-114
关键词	Amino acid enantioselective fluorination Lewis acid organocatalysis primary amine
ISSN号	0039-7911
通讯作者	徐利文
英文摘要	The fluorination reaction is an important organic transformation for asymmetric synthesis. In this article, we reported the determination of chiral primary amine–based multicatalyst systems for enantioselective fluorination of β-ketoester. Studies on the enantioselective organocatalytic fluorination promoted by cinchona alkaloid–derived chiral primary amines in the absence of various co catalysts revealed that the combined metal salts and organocatalysts resulted in poor conversion and enantioselectivities, whereas the combinational use of L-leucine and QN-NH₂ as dual primary amine catalysts led to the determination of a novel dual organocatalyst with promising catalytic activity. On the basis of these results, we revealed that the steric environment of the chiral enamine intermediate formed by the condensation of β-ketoester with the chiral primary amine is most responsible for the observed enantioselectivity.
学科主题	物理化学与绿色催化
收录类别	SCI
资助信息	the National Natural Science Foundation of China (Nos. 20973051;21173064;51203037);Zhejiang Provincial Natural Science Foundation of China (Q12B020037);Education of Zhejiang Province (Y200803767);Program for Excellent Young Teacher in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014)
语种	英语
WOS记录号	WOS:000325514400010
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/19284]
专题	兰州化学物理研究所_OSSO国家重点实验室
作者单位	1.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou, Zhejiang, Peoples R China 2.Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117548, Singapore 3.Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117548, Singapore 4.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
推荐引用方式 GB/T 7714	Shang, Jun-Yan,Li L,Lu YX,et al. Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems[J]. Synthetic Communications,2014,44(1):101-114.
APA	Shang, Jun-Yan,Li L,Lu YX,Yang KF,&Xu LW.(2014).Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems.Synthetic Communications,44(1),101-114.
MLA	Shang, Jun-Yan,et al."Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems".Synthetic Communications 44.1(2014):101-114.